1-Phenylpiperazine → [2-(4-Phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl]propylamine

HRID 2240104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240104
Cl[C:2]1[N:3]=[C:4]([CH2:11][CH2:12][CH2:13][NH2:14])[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.[C:15]1([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCOCC1>[C:15]1([N:21]2[CH2:26][CH2:25][N:24]([C:2]3[N:3]=[C:4]([CH2:11][CH2:12][CH2:13][NH2:14])[C:5]4[S:10][CH2:9][CH2:8][C:6]=4[N:7]=3)[CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

4

Edukt 2

HCID 70961-PhenylpiperazineHCID 86632801(2-Chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)propylamine

Produkt 1

HCID 68440117[2-(4-Phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl]propylamineAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

9.7 g (42.3 mmol) of 2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)propylamine (VIII) and 25.7 mL (169.2 mmol) of 1-phenylpiperazine (III) are placed in 200 mL of dioxane (carried out in 10 batches), then reacted for 1 hour at 160° C. in the microwave. The reaction mixture is concentrated by evaporation, the residue is combined with 250 mL of water. Then the mixture is suction filtered, washed with water, and dried. The residue is stirred with acetonitrile, then recrystallized from isopropanol. 8.3 g of the product (I) (55%) is obtained as a powder (m.p. 121° C.). 1H NMR (400 MHz, DMSO): 7.22 (2H, t); 6.97 (2H, d); 6.79 (1H, t); 6.43 (2H, t); 3.81-3.69 (4H, m); 3.37-3.19 (4H, m); 3.19-3.09 (4H, m); 2.99 (2H, t); 1.62-1.47 (2H, m); 0.87 (3H, t).

Aufarbeitung

  1. customthen reacted for 1 hour at 160° C. in the microwave
  2. concentrationThe reaction mixture is concentrated by evaporation
  3. filtrationfiltered
  4. washwashed with water
  5. customdried
  6. customrecrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-ba4e46e9cee543e589d2862cc5460b83
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723341B2

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